It has been a “season of regret,” with corporate miscues and apologies rampant: Toyota’s recall, NBC’s Jay Leno/ Conan O’Brien scheduling gaffe and final recognition of Time Warner’s AOL blunder. If only there were a do-over. What are the biggest mistakes in Jewish history? We asked Rabbi Charlie Buckholtz, senior editor at the Shalom Hartman Institute and author, to describe regrettable moments in Jewish history where a do-over might have been helpful. Tell us what you think. Any regrets on our regrets? E-mail us at connect@jinsider.com.

Two Kinds of Mistakes

There are two kinds of mistakes — necessary/constructive and unnecessary/destructive. The former are choices that reflect something noble and essential about our humanity and advance human and Jewish destiny even though, at the time, they may appear to contradict not only God’s will but also our own enlightened self-interest. These are rebellious-type decisions we would nevertheless not want to take back. Rather, we tend to take a kind of weary pride in them. The template for this kind of mistake is eating from the Tree of Knowledge, aka, the mistake that gave birth to human history. This mistake clearly expresses a deep human value position: the prioritization of free choice, curiosity and learning — evolution — to stasis of any kind, even the stasis of spiritual bliss in Eden. To regret it would be to regret our own existence. Not so Jewish.

In contrast, unnecessary/destructive mistakes metastasize into corrosive regret. They are the choices we make based on failings of courage and consciousness, the triumph of the voice inside us that is small, petty and afraid for all the wrong reasons. They are the moments when we find ourselves shouting at the movie screen of our own lives and the lives of those who came before us. “You really do not want to do that!” Consider this a festival of our ancestors’ blooper reels. They lived it and recorded it; the least we can do is listen and learn. Please turn off your cell phones.

Moses Smashing the Tablets

According to the Talmud, the tablets Moses first brought down from Sinai were like a marriage contract between the Jewish people and their spiritual betrothed: God. When the people started worshiping the Golden Calf, they rendered the contract null and void. Moses, therefore, was well within his rights to smash them. Still, is it not the task of spiritual leadership to remind us of our deepest connections and commitments precisely in those moments when despair and paranoid pettiness have taken hold? Who knows what wisdom those first tablets held? Who knows what further tragic failings they could have helped us to avoid.

The Spies

The 12 heads of the Israelite tribes return from a mission to scout out the Promised Land and apprise the people of their findings: “Ten of the men began to tell about the giants and how fearful they were. They told of large cities with high walls around them. ‘We cannot go into this land,’ they said. ‘We were just like grasshoppers in our own sight, and also in the sight of the people there.’” We get it: You guys were scared. You had spent most of your life as slaves and the rest fed on manna and protected by miracles. You don’t exactly know your way around a phalanx and you can barely tell which end is up on a spear. Still ... you were all we had! We needed you to rise to the occasion, to hold a space for your personal anxiety without letting it infect your public speech. You could have saved us 37 years of desert bickering and backstabbing, a distinctly Jewish plague whose deep, festering power lives with us to this day.

The Rejection of Jesus

Calm down — not that rejection of Jesus. With regard to him not being God, messiah, etc, we’re still on solid Judaic ground. But the Talmud reports another moment, a quiet encounter between an esteemed rabbinic teacher in the midst of personal prayer and a troubled but devoted student seeking solace and a willing ear for his penitent soul. Rather than setting aside his prayer and rising to embrace his returning disciple, the teacher waved an ambiguous hand gesture that the student took as a final rejection. In his despair, he turned to wantonness and idolatry. Of interest here is not the story’s historical accuracy, but its boldly self-critical mood. Remarkably, the compilers of the Talmud found it important to record a nagging sense of regret in their predecessors’ initial response to Christianity: Could things have gone differently? For according to the Talmud the student was Jesus, and the rest is history.

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